Water-insoluble azo-dyestuffs and fiber dyed therewith



Patented Apr. 30, 1935 Erwin Hoffa and Fritz Miiller, Frankfort-on-the l Main, Germany, assignors to General Aniline Works, Inc., New York, N. Y., a corporation of Delaware No Drawing. Application October 5, 1931, Serial No. 567,1 32.- In Germany October 10, 1930 dyestuffs obtained from l-amino-Z-chloro-S-trifluoromethylbenzene, in general are faster to light than the corresponding dyestufis from 1 amin'o-z-chlorobenzene. J I

The dyestuffs obtainable by our process possess valuable vivid orange to scarlet tints. The fastmess to light "of their dyeings when produced on cotton is in general, but especially in the case of the dyestuffs prepared from l-amino-5-trifluoromethylbenzene, and/or l-amino-Z-chloro- ;,5-trifluoromethylbenzene, a good one. In the tween grades 6 and. 7 of the norms for Lichtechtbelt of the Echtheitskornmission der Fachgruppe fiir Chemie der Farbenund Textilindustrie im Verein Deutscher Chemiker, 4th Edit, 1928 (reprinted in Schultz, Farbstofftabellen, vol. 1 1931, page XXXI et seq.)-.

Furthermore, it is noticeable that our new dyestuffs possess a rather high fastness to boiling with water and to Washing. Their fastness in 5.,of the norms for Kochechtheit of the beforesaid Echtheitskommission (Schultz, Farbstofftabellen, vol. 1, 1931, page XXXII) 40 0f the presence of the strongly negative substituent CFs, as it is known that compounds containing the trichloromethyl group are very sensitive to chemical influences.

The dyestuffs canbe produced in substance,

substrata which are adapted for the production of lakes.

The dyestuffs obtained by this invention cor- 56 respond with the following general formula:

wherein R1 represents abenzene radical which is case of the before mentioned bases it lies be- 7th Edit, u

this respect lies in general between grades 4 and This latter fact could not be expected in view' on the fiber, or in the presence of any of the usual the nitro group, R2 represents a radical of the benzene or naphthalene series which must not contain sulfonic or carboxylic acid groups.

The following examples serve to illustrate the invention, but they are not intended to limit it thereto: 7

(1) grams of cotton yarn are treated with the grounding liquor hereinafter described for half -an-hour, well freed from water by centrifuging or wringing and developed for halfA-an-hour.

in the diazo-solution described. The dyed yarn is well rinsed, soaped at boiling temperature and dried.

' (a) The grounding liquor is prepared asfollows: 5 grams of 2'3"-hydroxynaphthoyl- 2 -meth- V oxy-l-aniline are well made into; a

paste with 10 cc of Turkey red oil and 10 cc of caustic soda solution, dissolved in boiling water and, after cooling, mixed with 5 cc of formaldehyde of 30 per cent. strength and the whole is'made up to .1 liter.

(b) The developing bath is prepared as follows: 1.92 grams of 1 -amino-2-methoXy-5-trifluoromethylbenzene are diazotized in the cold with of hydrochloric acid of 20? B.

V and 3 0.75 grams of sodium nitrite. The diazo-solution is neutralized with about 2 grams of sodium acetate and after addition of 25 grams of dissolved sodium chloride, the

whole is made up to 1 liter.

The'dyeing is a scarlet of good fastness properties. The dyestuff obtained has the following formula: v

moo

OH \GF;

moo

trifluoromethylbenzene, there is slowly run,

; 1,999,610 UNITED STATES PATENT OFFICE WATER-INSOLUBLE AZO-DYESTUFFS AND FIBER DYED THEREWITH (2) Into a diazo-solution, prepared in the usualmanner from 19.6 parts of l-amino-2-chloro-5- while well stirring, a solution of 29.5 parts of 2'3- 2. The water insoluble azo-dyestufi of the folhydroxynaphthoyl-2-methoxy-l-aminobenzene in lowing formula:

a caustic soda solution to which there has been added the quantity of sodium acetate necessary l ness properties.

The dyestufi obtained h as the following condyeing a reddish-orange shade and being disstitution:

o1 tinguished by 1ts good fastness properties, particularly by its good fastness to light. N=N 3. The water insoluble azo-dyestufi of the following formula: i 1 H CF 01 (JO-NH 0E CF:

H O The following dyestuffs, among others, are capable .of production in accordance with this invention? Active coupling component Passive coupling component Shade" 1 l-arnino-3-trifluoromethylbenzene 2,3-hydroxynaphthoyl-l-amino-2-niethoxy-4-chloroben- Orange.

- zene. 2 1-amino-3-trifl110r0-methy1benzeno 2,3'-l1ydroxynaphthoyl-1-amino-2-methoxybenzene Do. 3 l-amino-3trifiuoro-methylbenzene. 2',3-hydroxynaphthoy1-l-amino-2-methoxy-5-chloroben- Reddish zene. orange. 4 l-amino-3-trifluoro-methylbenzene- 2,3-hydroxynaphthoyl-l-aminmZ-methyl-imethoxyben- Brownish zene. orange. 5 l-amino-3-trifluoro-rnethylbenzene. 2,3111- hyglroxynaphthoyl 1 amino 2.5 dimethoxy 4 Do.

0 oro enzene. g 6 1-amino-3-trifluoro-methy1benzene 2,3-hydroxynaphthoyl-l-amino-4-methoxybenzene Yellolwsh V Y scar e 7 l-amino-Z-methoxy-S-trifluoromethyl-benzene 2,3]-)hydroxynaphthoyl-1amino-2.5-dimethoxy-4-cl11o- Scarlet.

ro enzene. 8 1-amino-2-cl11oro-5-trifluoromethyl-benzene 2,3'-hydroxynaphthoyl-l-amino-2-methoxybenzene Reddish orange. 9 l-amino-2-chloro-5-trifluorometl1ylbenzene 2',3-hydroxynaphthoyl-l-amino-i-methoxybenzene Orange. 10 1-amino-2-ch10ro-5-trifluoromethylbenzene 22g-hydroxynaphthoyl-l-amino-2-methoxy-4-chloro- Scarlet.

. enzene. 11 1-amino-2chloro-5-trifluoromethylbenzene 2',3-hydroxynaphthoyld aminobenzenen.L Reddish' orange. 12 l-amino-2-chloro-5-trifluoromethylbenzene 2,3-hydroxynaphthoyl-l-amino-2-methylbenzene 'Yellolwtisth scare o red-or- V I ange. 13 l-amino-2-chloro-5-trifluoromethylbenzene 221151-hydroxynaphthoyl-1-amino-2-methoxy-5-chloro- Do.

enzene. 14 1-an1ino-2chl0ro-5-trifluoromethylbenzene 2,3-hydroxynaphthoyl-l-amino-2'ethoxybenzene Orange. 15 l-amino-2chloro-5-trifiuoromethylbenzene 2,3-hydroxynap11thoyl-l-amino-2-inethyl-4-chlorobenzene Yellowlislz,

- scar e t o r e dorange. 16 l-amin0-2-chloro-5-trifluoron1ethylbenzene 2,3'-hydroxynaphthoyl-l-aminonaphthalene Brovlvlnish ye ow- Y red. 1 17 l-amino-Z-chloro-fi-trifluoromethylbenzene 2',3'-hydroxynaphthoyl-2-arninonaphthalene Reddish- 1 I r orange. 18 1-a1nino-2-nitro-4-trifluoromethylbenzone 2,3-hydroxynaphthoyl-l-aminobenvene Orange.

We claim: dyeing a reddish-orange shade and being dis- 1. The water-insoluble azo-dyestuifs of the following general formula:

wherein X stands for hydrogen 0 r methoxy, dyeingrvivid orange shadesand being distinguished ye a Orang by their good fastness properties, particularly by by it oo fastn ss p t s, P

;.their good fastness to light.

ticularly by its good fastness to light.

4. The water-insoluble azo-dyestufi of lowing formula:

tinguished by its good fastness properties, par

the folits good fastness to light.

5. Fiber dyed with the azo-dyestuffs as claimed 8. Fiber dyed with the azo-dyestuff as claimed in claim 1. in claim 4.

6. Fiber dyed with the azo-dyestuff as claimed ERWIN I-IOFFA.

in claim 2. V FRITZ MULLER.

7. Fiber dyed with the azo-dyestuff as claimed in claim 3. 

